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© Alison Buck/Getty Images for TheWrap Chris Sacca. Alison Buck/Getty Images for TheWrap
  • Chris Sacca's friend rejected an early job at Stripe, now a $95 billion company.
  • The billionaire investor passed on Airbnb, Snapchat, Pinterest, and Dropbox.
  • Sacca was worried about culpability, market size, originality, and competition.
  • See more stories on Insider's business page.

Investor Chris Sacca tweeted on Saturday that one of his friends turned down an early role at Stripe, the payments group valued at $95 billion in a funding round last week.

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'He was considering a job with a couple of Irish dudes named @Patrickc & @collision,' the Lowercase Capital founder and former 'Shark Tank' star said, referring to Stripe cofounders Patrick and John Collison. 'He opted for something else. Whoops.'

Sacca used the anecdote as a springboard to discuss how investors inevitably overlook opportunities, and to highlight some of his biggest misses.

'I had nauseatingly confident explanations for why Airbnb, Dropbox, Snapchat, Pinterest, and other startups like them would never be able to pay back a $25,000 check,' he tweeted. 'Ugh. My bad.'

Airbnb boasts a market capitalization of about $120 billion today. Snapchat, Pinterest, and Dropbox have market caps of around $84 billion, $45 billion, and $11 billion respectively.

Sacca missed out on billions of dollars by not backing those companies. He's explained why he passed on each of them in previous tweets.

The venture capitalist rejected Airbnb because he feared a guest would be murdered and the blood would be on the home-rental platform's hands. He turned down Snapchat because he worried the messaging app would only be used to share risqué images.

Sacca declined to back Dropbox because he was certain Google Drive would crush the upstart file-hosting service. Finally, he 'yawned' at the prospect of investing in Pinterest, dismissing online pinboards as nothing new.

The angel investor missed a trick with those companies, but he made the right call on other startups including Uber, Twitter, and Instagram. Still, he recognizes how frustrating and demoralizing it can be to miss out on making a fortune.

'So much of life is resilience despite hindsight,' he tweeted on Saturday.